Massdrop should land somewhere in the middle with this.
I understand a nice capital injection of cheap merch for the org (that we all enjoy), but I also think the price is asking a bit much for the "walking billboard".
These should be a 5 dollar (for the 5 year mark) add on item (so we have to buy something else first, which you know we want to anyways) so that we everybody wins. I would probably buy both colors if they were $5.
Side bar: I don't know what size to order either. I can wear anything from L to XXL depending on how the factory cut them that day..I have had size deviations on the same brand and T shirt model when ordering online.